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Stewart

$109+ Cheap flights from Pittsburgh to New Windsor (PIT - SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SWF
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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Cheap flight deals from Pittsburgh to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 28, 2025.

Round-trip from

$239
(Mytrip)

One-way from

$109
(Mytrip)

Popular in

November

Cheapest in

April

Average price

$170
From Pittsburgh to New Windsor Stewart
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One-way flight from Pittsburgh to New Windsor Stewart
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Highest demand for flights based on searches. 15% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Pittsburgh to Stewart

Cheapest flights from Pittsburgh to Stewart
Explore the most affordable flight options available from Pittsburgh to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.

This Mytrip deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:36 pmPIT - SWF
1 stop5h 13mMultiple Airlines
Mon 10/2011:01 amSWF - PIT
1 stop12h 21mMultiple Airlines
Deal found 7/25$239
This Mytrip deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/319:00 amPIT - SWF
1 stop9h 00mAllegiant Air
Mon 9/112:17 pmSWF - PIT
1 stop10h 53mAllegiant Air
Deal found 7/26$287
This KAYAK deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/149:08 pmPIT - SWF
1 stop15h 40mBreeze Airways
Thu 8/217:52 pmSWF - PIT
2 stops16h 57mBreeze Airways
Deal found 7/27$702

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh to Stewart that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 28, 2025.
Use the filters below to find and compare flights from Pittsburgh to New Windsor that are best for you.

Fly from

Pittsburgh

Fly to

Stewart

Route

Depart

Return

Price

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 10/17

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

Mon 10/20

11:01 am-11:22 pm

1 stop12h 21m

$239

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Sun 8/31

9:00 am-6:00 pm

1 stop9h 00m

New Windsor Stewart

Mon 9/1

12:17 pm-11:10 pm

1 stop10h 53m

$287

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 8/14

9:08 pm-12:48 pm

1 stop15h 40m

New Windsor Stewart

Thu 8/21

7:52 pm-12:49 pm

2 stops16h 57m

$702

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Mon 8/11

6:20 am-7:06 pm

1 stop12h 46m

$109

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 8/7

6:00 pm-10:29 am

1 stop16h 29m

$133

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Sun 8/24

9:08 pm-12:48 pm

1 stop15h 40m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Best time to book a flight from Pittsburgh to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Pittsburgh with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Pittsburgh to New Windsor

What is the cheapest month to book a flight from Pittsburgh to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Pittsburgh to New Windsor (average of $109). Flying from Pittsburgh to New Windsor in August is currently the most expensive (average of $206). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PIT to SWF?

Find hourly flight availability from Pittsburgh to Stewart. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 28, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pittsburgh to New Windsor as you normally would.

Reviews of airlines servicing Stewart

Get insights into the airlines that provide service to Stewart. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Stewart. Reviews last updated July 28, 2025.
Get a feel of what it's like to fly with Breeze Airways and Allegiant Air from Pittsburgh to New Windsor by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
190 reviews

Crew

8.7

Food

6.7

Boarding

8.3

Overall

8.0

Comfort

8.1

Entertainment

6.6

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
190 reviews
Breeze Airways
8.0
Very good
190 reviews

Crew

8.7

Food

6.7

Boarding

8.3

Overall

8.0

Comfort

8.1

Entertainment

6.6

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Allegiant Air
7.2
Good
702 reviews
Breeze Airways
8.0
Very good
190 reviews

Crew

8.7

Food

6.7

Boarding

8.3

Overall

8.0

Comfort

8.1

Entertainment

6.6

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Pittsburgh to Stewart that include hotel bookings?

    Yes. In addition to deals on Pittsburgh to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pittsburgh to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pittsburgh to Stewart.

  • Can I find deals for business class flights from Pittsburgh to Stewart?

    Yes. Cheapflights offers flight deals from Pittsburgh to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pittsburgh to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Pittsburgh to New Windsor (average of $109). Flying from Pittsburgh to New Windsor in August is currently the most expensive (average of $206). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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